Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives
Zhang, Chao-Bo1; Liu, Yang1; Liu, Zheng-Fen1; Duan, Sheng-Zu1; Li, Min-Yan3; Chen, Wen1; Li, Yan2; Zhang, Hong-Bin1; Yang, Xiao-Dong1
2017-04-15
发表期刊BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷号27期号:8页码:1808-1814
摘要The synthesis of a series of novel 4-substituted 2,3,6,7-tetrahydrobenzo [1,2-b;4,5-b']difuran-1H-imidazolium salts is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. Results suggest that the 5,6-dimethyl-benzimidazole or 2-methyl-benzimidazole ring, and substitution of the imidazolyl-3-position with a 2-naphthylmethyl substituent or 2-naphthylacyl substituent, were important to the cytotoxic activity. Notably, 3-(2-Naphthylmethyl)-1-(2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-y1)methyl)-1H-5,6-dimethyl-benzimidazol-3-ium bromide (42) was found to be the most potent derivative against five human tumor cell lines with 1050 values of 1.06-4.34 mu M and more selective towards SMMC-7721, A549 and SW480 cell lines. 3-(2Naphthylacy1)-1-(2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-yl)methyl)-1H-2-methyl-benzimidazol- 3-ium bromide (37) showed higher selectivity to SMMC-7721 and MCF-7 cell lines with IC50 values 2.7-fold and 8.4-fold lower than DDP. Study regarding to the antitumor mechanism of action showed that compound 37 could induce cell cycle G1 phase arrest and apoptosis in SMMC-7721 cells. (C) 2017 Elsevier Ltd. All rights reserved.
关键词Tetrahydrobenzodifurans Imidazolium Salts Cytotoxic Activity Cell Cycle Apoptosis
资助信息Natural Science Foundation of China(21662043; Program for Changjiang Scholars and Innovative Research Team in University(IRT13095); Excellent Young Talents of Yunnan University; 21462049; 21332007; U1402227)
DOI10.1016/j.bmc1.2017.02.053
收录类别SCI
语种英语
WOS研究方向Pharmacology & Pharmacy ; Chemistry
WOS类目Chemistry, Medicinal ; Chemistry, Organic
WOS记录号WOS:000399262600033
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/51196
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Peoples R China
3.Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
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GB/T 7714
Zhang, Chao-Bo,Liu, Yang,Liu, Zheng-Fen,et al. Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2017,27(8):1808-1814.
APA Zhang, Chao-Bo.,Liu, Yang.,Liu, Zheng-Fen.,Duan, Sheng-Zu.,Li, Min-Yan.,...&Yang, Xiao-Dong.(2017).Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,27(8),1808-1814.
MLA Zhang, Chao-Bo,et al."Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 27.8(2017):1808-1814.
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